title: Enantioselective synthesis of α-nitro-δ-ketosulfones via a quinine-squaramide catalyzed conjugate addition of α-nitrosulfones to enones.
abstract: Conjugate addition of α-nitrosulfones to vinyl ketones in the presence of 0.2 mol% of a quinine-squaramide organocatalyst afforded α-nitro-δ-ketosulfones possessing a tetrasubstituted chiral center in excellent yield and enantioselectivity in most cases. This strategy also offers a facile and convenient entry into γ-sulfonylhydroxamates that are one carbon homologs of potent enzyme inhibitors.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400 076, India. irishi@iitb.ac.in.
authors.forename: Kalisankar
authors.initials: K
authors.lastname: Bera
authors.forename: Irishi N N
authors.initials: IN
authors.lastname: Namboothiri
mesh_terms: D000577:Amides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D006877:Hydroxamic Acids / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D020782:Matrix Metalloproteinases / Q000737:chemistry / Q000378:metabolism; D008968:Molecular Conformation; D011803:Quinine / Q000737:chemistry*; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000577:Amides; D002264:Carboxylic Acids; D004791:Enzyme Inhibitors; D006877:Hydroxamic Acids; D007659:Ketones; D013450:Sulfones; D011803:Quinine; D020782:Matrix Metalloproteinases